[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

EP0164879A1 - Compositions de polysiloxanes pour couches primaires - Google Patents

Compositions de polysiloxanes pour couches primaires Download PDF

Info

Publication number
EP0164879A1
EP0164879A1 EP85303185A EP85303185A EP0164879A1 EP 0164879 A1 EP0164879 A1 EP 0164879A1 EP 85303185 A EP85303185 A EP 85303185A EP 85303185 A EP85303185 A EP 85303185A EP 0164879 A1 EP0164879 A1 EP 0164879A1
Authority
EP
European Patent Office
Prior art keywords
component
group
primer composition
silicon
bonded
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP85303185A
Other languages
German (de)
English (en)
Other versions
EP0164879B1 (fr
Inventor
Kazuo Hirai
Takao Matsushita
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DuPont Toray Specialty Materials KK
Original Assignee
Toray Silicone Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Toray Silicone Co Ltd filed Critical Toray Silicone Co Ltd
Publication of EP0164879A1 publication Critical patent/EP0164879A1/fr
Application granted granted Critical
Publication of EP0164879B1 publication Critical patent/EP0164879B1/fr
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • the primer of this invention is appropriate for adhering curable silicone compositions, particularly heat curable, to the surfaces of various organic materials.
  • Silicone rubbers have an excellent heat resistance. For this reason, they have recently been used in a broad range of applications in which rubber elasticity is required at elevated temperatures.
  • silicone rubbers are more expensive than general-purpose synthetic rubbers and general-purpose plastics and have slightly inferior properties, e.g., initial mechanical properties, steam resistance and chemical resistance, etc., compared to some synthetic rubbers and plastics.
  • composite materials have been widely used in which the surface of a synthetic rubber or plastic is coated with a silicone rubber so the rubber or plastic material will not suffer from oxidative degradation by oxygen at elevated temperatures.
  • a primer composition has been developed which can tightly adhere curable silicone compositions and particularly heat-curable silicone rubber compositions to various synthetic rubbers, plastics, and to inorganic materials brought into contact with the silicone compositions during cure.
  • the primer composition is composed of three components.
  • Component (I) consists of component (A) or (B).
  • Component (A) consists ofyan organosilicon compound containing at least one epoxy group-containing monovalent hydrocarbon group, and at least one silicon-bonded lower alkenyl group or silicon bonded hydrogen atom in each molecule.
  • Component (B) consists of a mixture of (a) an organosilicon compound which possesses silicon-bonded hydroxyl and silicon-bonded lower alkenyl radicals or silicon-bonded hydrogen, and (b) an organotrialkoxysilane containing at least one epoxy group containing monovalent hydrocarbon group.
  • Component (II) comprises a trialkoxysilane or its partial hydrolysis product.
  • Component III comprises an organotitanate ester.
  • the present invention relates to a primer composition consisting essentially of Component (I) consisting of either (A) consisting of an organosilicon compound in which at least one A(RO) 2 Si group and at least one silicon-bonded lower alkenyl group or silicon-bonded hydrogen atom are present in each molecule where A is an epoxy group-containing monovalent hydrocarbon group and R is a lower alkyl group; or (B) consisting of a mixture of (a) an organosilicon compound which contains silicon-bonded hydroxyl group and silicon-bonded lower alkenyl group or silicon-bonded hydrogen atom, and (b) an organotrialkoxysilane with the general formula ASi(OR 1 ) 3 where A is as defined above and R is an alkyl group; Component II consisting essentially of a trialkoxysilane with the general formula R 2 Si(OR 3 ) 3 or its partial hydrolysis condensation product where R 2 is-a hydrogen atom or an organic group possessing an aliphatically unsaturated bond and R 3 is an alky
  • Component (I) is the principal component of the primer composition of the present invention. It forms a cured film that tightly adheres to the substrate by an alcohol-liberating condensation with component (II) in the presence of ambient moisture and in the presence of catalytically active component (III).
  • Component (I) consists of either component (A) or component (B).
  • Component (A) is an organosilicon compound in which at least one A(RO) 2 Si group and at least one silicon-bonded . lower alkenyl group or silicon-bonded hydrogen atom are present in each molecule.
  • A is an epoxy group-containing monovalent hydrocarbon group and R is a lower alkyl group.
  • Each molecule of component (A) preferably possesses at least 2 epoxy group-containing monovalent hydrocarbon groups with the general formula R 6 is an arbitrary divalent organic radical for which concrete examples are the phenylene group, hydroxylated hydrocarbon radicals, the chloroethylene group, the fluoroethylene group, -CH 2 0CH 2 CH 2 CH 2 -, -CH2CH2OCH2CH2-, -CH 2 CH 2 OCH(CH 3 )CH 2 - and -CH 2 OCH 2 CH 2 OCH 2 CH 2 -.
  • Other examples of A are-the beta-(3,4-epoxycyclohexyl)ethyl group and the gamma-(3,4-epoxycyclohexyl)propyl group.
  • R are methyl, ethyl, normal-propyl, isopropyl, hexyl, and methoxyethyl.
  • the methyl group is preferred.
  • Concrete examples of the silicon-bonded lower alkenyl group are allyl, 1-butenyl and isopropenyl.
  • Typical examples of the organosilicon compound include organosilanes and organopolysiloxanes. The molecular configuration of such an organopolysiloxane is straight chain, branched chain, cyclic or network.
  • the degree of polymerization is equal to or greater than 2; however, it is preferably a degree of polymerization corresponding to an oligomer.
  • component (A) are copolymer resins constituted of 52.5 mol% MeSiO 1.5 units, 5 mol% ViSiO 1.5 units, 40 mol% Me ⁇ SiO units and 2.5 mol% units, and copolymer resins constituted of 50 mol% MeSiO 1.5 units, 40 mol% MepSiO units, 4.7 mol% MeHSiO units, 2.3 mol% Me 3 SiO 0.5 units and 3.0 mol% units (Me is the methyl group, Et is the ethyl group, Vi is the vinyl group and ⁇ is the phenyl group).
  • organosilicon compounds comprising component (A) can be produced by the alcohol-liberating condensation of an organotrialkoxysilane in which, for example, the organic group is the epoxy group-containing monovalent hydrocarbon group, with an organopolysiloxane possessing silicon-bonded hydroxyl groups at elevated temperatures of 150 to 160°C for several hours.
  • the component (B) which may constitute component (I) is a mixture of (a) an organosilicon compound which possesses silicon-bonded hydroxyl and silicon-bonded lower alkenyl or silicon-bonded hydrogen and (b) an organotrialkoxysilane with the general formula ASi(OR 1 ) 3 (A carries the preceding definition and R is an alkyl group).
  • the organosilicon compounds comprising component (a) are typically organosilanes and organopolysiloxanes.
  • the molecular configuration of such an organopolysiloxane is straight chain, branched chain, cyclic or network.
  • the degree of polymerization is equal to or greater than 2; however, it is preferably the degree of polymerization corresponding to an oligomer. At least 1 silicon-bonded hydroxyl group and at least 1 silicon-bonded lower alkenyl group or silicon-bonded hydrogen atom are present in each molecule; however, equal to or greater than 2 of . each are preferred from the standpoint of adhesion.
  • organosilicon compounds comprising component (a) are organopolysiloxane resins constituted of 52.5 mol% MeSiO 1.5 units, 5 mol% ViSiO 1.5 units, 35 mol% Me ⁇ SiO units and 5 mol% HO(Me) 2 SiO 0.5 units, and organopolysiloxane resins constituted of 3 mol% (Me) 3 SiO 0.5 units, 4 mol% HO(Me) 2 SiO 0.5 units, 10 mol% MeHSiO units and 83 mol% MeSiO 1.5 units.
  • Me, ⁇ and Vi carry their definitions from above.
  • Examples of A in the general formula ASi(OR 1 ) 3 for organotrialkoxysilanes comprising component (b) are the same as given for component (A) and examples of the alkyl group R 1 are the same as R described for component (A).
  • component (a) is arbitrary; however, component (b) is preferably present at 0.5 to 3 mol relative to 1 mol component (a).
  • Component (II) undergoes an alcohol-liberating condensation with component (I) in the presence of ambient moisture and catalytically active component (III) to form a cured film adhering to the substrate.
  • R 2 in general formula R 2 Si(OR 3 ) 3 is a hydrogen atom or an organic group possessing an aliphatically unsaturated bond. Concrete examples of the organic group possessing an aliphatically unsaturated bond are alkenyl, acryloxyalkyl and methacryloxyalkyl groups. R is an alkyl group.
  • trialkoxysilanes are triethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(beta-methoxyethoxy)silane, gamma-methacryloxypropyltriethoxysilane, gamma-acryloxypropyltrimethoxysilane, allyltrimethoxysilane and allyltriethoxysilane.
  • the partial hydrolysis products of these trialkoxysilanes may also be employed.
  • Component (III) is an organotitanate ester with a catalytic activity such that the mixture of components (I) and (II) cures in the presence of ambient moisture and rapidly air-dries.
  • component (III) are tetra(propyl)titanate, tetra(normal-butyl)titanate, butyl titanate dimer, tetra(2-ethylhexyl)tianate, the polycondensation products of these titanates, and titanium chelate compounds, such as titanium bisacetylacetonate, dibutoxytitanium bisacetylacetonate, titanium lactate ethyl esters ' and titanium triethanolaminate.
  • component (II) is preferably present at 5 to 500 weight parts per 100 weight parts of component (I) while component (III) is present at 1 to 200 weight parts per 100 weight parts component (I).
  • the primer composition of the present invention is readily produced by simply mixing the preceding components (I) to (III) with each other to homogeneity.
  • Inorganic additives such as fumed silica, fumed silica whose surface has been hydrophobicized with organosilane, and extremely fine silica powder such as fine quartz powder; thermal stabilizers such as red iron oxide, cerium oxide, cerium hydroxide; aliphatic acid salts of cerium and aliphatic acid salts of iron; pigments such as titanium dioxide and carbon black; and organic solvents such as rubber volatile oil, toluene, xylene, ethanol, and trichloroethane may be optionally added.
  • the primer composition produced in the present invention may be cured by coating it on the adherend and air-drying for 10 minutes or longer followed by the application and curing of the curable silicone rubber composition or curable silicone resin composition.
  • the primer composition is optionally baked to secure a reliable cure.
  • the primer composition of the present invention is coated on the surface of an organic material such as a synthetic rubber, e.g., ethylene-propylene rubber, isoprene rubber, chloroprene rubber, Hypalon, butyl rubber, chlorinated butyl rubber, etc., or a plastic, e.g., polyethylene resin, polypropylene resin, polyester resin, acrylic resin, phenol resin, epoxy resin, etc., or is coated on the surface of an inorganic material such as glass, metal or ceramic, etc., and a curable silicone composition and particularly a heat-curable silicone rubber composition or a heat-curable silicone resin composition is applied, and then cured in order to tightly and durably adhere the cured silicone material to the various materials.
  • an organic material such as a synthetic rubber, e.g., ethylene-propylene rubber, isoprene rubber, chloroprene rubber, Hypalon, butyl rubber, chlorinated butyl rubber, etc.
  • a plastic e.g.,
  • an organopolysiloxane with general formula (1) 100 parts are mixed with 40 parts gamma-methacryloxypropyltriethoxysilane and 50 parts di(normal-butoxy) titanium bisacetylacetonate to homogeneity and then dissolved in normal-hexane to obtain a 15% solution.
  • the resulting primer composition is coated on test pieces (30 mm (width) X 100 mm (length) X 3 mm (thickness)) of vulcanizates of an ethylene-propylene terpolymer rubber (EPDM) composition and an EPDM-silicone rubber blend rubber composition (SE4306 from Toray Silicone Co., Ltd.) and then air-dried at room temperature for 40. minutes.
  • EPDM ethylene-propylene terpolymer rubber
  • SE4306 EPDM-silicone rubber blend rubber composition
  • a silicone rubber composition (SH1135u from Toray Silicone Co., Ltd.) which contains 0.5% 2,3-dimethyl-2,5-di(tertiary-butylperoxy)hexane as the vulcanization agent is adhered in a thickness of 3 mm to the above primer composition and then cured at a temperature of 170°C under an elevated pressure of 25 kg/cm 2 for 10 minutes. Test pieces are thus obtained in which the silicone rubber is tightly adhered on the above-mentioned adherend material. The test piece is repeatedly bent at its center 1000 times at an angle of 90°; however, the silicone rubber could not be peeled off from the rubber adherend.
  • primer composition P-1 tetra(normal-butyl)titanate
  • primer composition P-2 tetra(normal-butyl)titanate
  • the above primer compositions are coated on test pieces (30 mm (width) X 100 mm (length) X 3 mm (thickness)) of vulcanizates of an ethylene-propylene terpolymer rubber (EPDM) composition, an EPDM-silicone rubber blend rubber composition (SE-4306 from Toray Silicone Co., Ltd.) and a chloroprene rubber composition and on test pieces of a poly ethylene resin solid material.
  • EPDM ethylene-propylene terpolymer rubber
  • SE-4306 EPDM-silicone rubber blend rubber composition
  • the resulting primer compositions are air-dried at room temperature for 60 minutes or baked at 80°C for 60 minutes.
  • a silicone rubber composition (SH-52u from Toray Silicone Co., Ltd.) containing 0.5% 2,3-dimethyl-2,5-di(tertiary-butylperoxy)hexane is adhered in a thickness of 4 mm on the above primer compositions and then cured at a temperature of 170°C under an elevated pressure of 25 kg/cm 2 for 10 minutes. Test pieces are thus produced in which the silicone rubber is tightly adhered to the adherend material.
  • the silicone rubber layer was subjected to a tensile peeling force at 180° from the test sheet in which the silicone rubber was adhered to the adherend sheet. The results are reported in Table 1.
  • Primer compositions P-1 and P-2 of Example 2 are coated on test pieces (30 mm (width) X 100 mm (length) X 3 mm (thickness)) of the vulcanizates of an EPDM rubber composition and of SE4306 and then air-dried at room temperature for 60 minutes.
  • An addition-curable liquid silicone rubber composition (SE6706 from Toray Silicone Co., Ltd.) is adhered in a thickness of 2 mm on the preceding primer coat surfaces and then cured at a temperature of 150°C under an elevated pressure of 25 kg/cm 2 for 5 minutes. Test sheets are thus obtained in which the silicone rubber is tightly adhered to the above-mentioned adherend materials. These test sheets are examined by the same adhesion test as in Example 1. The results are 100% cohesive failure in all test sheets.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
EP85303185A 1984-05-04 1985-05-03 Compositions de polysiloxanes pour couches primaires Expired EP0164879B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP59089952A JPS60233153A (ja) 1984-05-04 1984-05-04 プライマ−組成物
JP89952/84 1984-05-04

Publications (2)

Publication Number Publication Date
EP0164879A1 true EP0164879A1 (fr) 1985-12-18
EP0164879B1 EP0164879B1 (fr) 1988-08-10

Family

ID=13985032

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85303185A Expired EP0164879B1 (fr) 1984-05-04 1985-05-03 Compositions de polysiloxanes pour couches primaires

Country Status (5)

Country Link
US (1) US4598134A (fr)
EP (1) EP0164879B1 (fr)
JP (1) JPS60233153A (fr)
CA (1) CA1244182A (fr)
DE (1) DE3564281D1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0306302A2 (fr) * 1987-09-04 1989-03-08 Cogent Limited Composition et procédé pour la fabrication d'un revêtement résistant au rayage
FR2629089A1 (fr) * 1988-03-24 1989-09-29 Rhone Poulenc Chimie Diorganopolysiloxane porteur a la fois de radicaux vinyle et de radicaux organique epoxy-fonctionnel
EP0500115A1 (fr) * 1991-02-21 1992-08-26 Dow Corning Corporation Composition de silicone pour couches primaires
GB2316079A (en) * 1996-08-13 1998-02-18 Gen Electric Primer composition for one-part RTV compositions
WO2008013521A1 (fr) * 2006-07-25 2008-01-31 Hewlett-Packard Development Company, L.P. Systèmes d'imprimante laser, éléments de transfert intermédiaire, couches primaires pour éléments de transfert intermédiaire et compositions de couches primaires

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62236880A (ja) * 1986-04-07 1987-10-16 Toray Silicone Co Ltd プライマ−組成物
JPS62280279A (ja) * 1986-05-28 1987-12-05 Toray Silicone Co Ltd プライマ−組成物
JPH0791527B2 (ja) * 1988-03-16 1995-10-04 信越化学工業株式会社 プライマー組成物
CA2055957A1 (fr) * 1990-12-18 1992-06-19 Edwin R. Evans Compositions a base de silicone vinyle, termine par le groupe silanol, agents pour le traitement de charges
US5213617A (en) * 1991-06-13 1993-05-25 Dow Corning Corporation Primer for silicone substrates
US5238708A (en) * 1991-06-13 1993-08-24 Dow Corning Corporation Primer for silicone substrates
JP3377534B2 (ja) * 1992-05-12 2003-02-17 ジーイー東芝シリコーン株式会社 熱定着用シリコーンゴムローラ
US5280098A (en) * 1992-09-30 1994-01-18 Dow Corning Corporation Epoxy-functional silicone resin
JP2922416B2 (ja) * 1994-02-15 1999-07-26 信越化学工業株式会社 プライマー組成物
DE19702704A1 (de) 1997-01-25 1998-07-30 Roland Dipl Phys Dr Goebel Haftfeste und feuchtestabile Legierungs-Kunststoff-Verbundschicht und Verfahren zu ihrer Herstellung
JP4639360B2 (ja) * 2000-03-31 2011-02-23 東レ・ダウコーニング株式会社 プライマー組成物、その製造方法および接着方法
JP5037243B2 (ja) * 2007-07-06 2012-09-26 富士フイルム株式会社 界面結合剤、該界面結合剤を含有するレジスト組成物、及び該界面結合剤からなる層を有する磁気記録媒体形成用積層体、並びに該界面結合剤を用いた磁気記録媒体の製造方法、及び該製造方法により製造された磁気記録媒体
JP5470809B2 (ja) * 2008-11-13 2014-04-16 凸版印刷株式会社 積層体の製造方法
EP2516570B1 (fr) 2009-12-23 2017-01-25 DSM IP Assets B.V. Procédé pour activer des surfaces de caoutchouc silicone afin d'améliorer les propriétés de mouillage et d'adhésion
BR112013007656B1 (pt) * 2010-09-30 2020-08-25 Abb Schweiz Ag composição iniciadora de silicone, seus usos e seu método de produção

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3772122A (en) * 1970-04-09 1973-11-13 Dow Corning Primer for adhesion of silicone rubber to metal
FR2321523A1 (fr) * 1975-08-19 1977-03-18 Toray Silicone Co Compositions d'organopolysiloxane vulcanisables presentant une adherence amelioree
FR2353597A1 (fr) * 1976-06-02 1977-12-30 Toray Silicone Co Compositions durcissables en deux parties presentant des proprietes d'adherence ameliorees sur divers substrats
GB2068397A (en) * 1980-01-21 1981-08-12 Toray Silicone Co Silicone compositions for adhesion and method for adhering silicone rubber to a substrate
EP0044672A1 (fr) * 1980-07-17 1982-01-27 Toray Silicone Company Limited Promoteurs d'adhérence à base d'une résine phénylsiloxane et d'un polysiloxane ayant des groupes vinyliques
EP0044673A1 (fr) * 1980-07-11 1982-01-27 Toray Silicone Company Limited Promoteurs d'adhérence contenant des résines phénylsiloxanes

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5126364A (fr) * 1974-08-29 1976-03-04 Japan Exlan Co Ltd
JPS5852350A (ja) * 1981-09-21 1983-03-28 Toray Silicone Co Ltd プライマ−組成物
DE3209755A1 (de) * 1982-03-17 1983-09-22 Wacker-Chemie GmbH, 8000 München Verfahren zum verstaerken des haftens von organopolysiloxanelastomeren

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3772122A (en) * 1970-04-09 1973-11-13 Dow Corning Primer for adhesion of silicone rubber to metal
FR2321523A1 (fr) * 1975-08-19 1977-03-18 Toray Silicone Co Compositions d'organopolysiloxane vulcanisables presentant une adherence amelioree
FR2353597A1 (fr) * 1976-06-02 1977-12-30 Toray Silicone Co Compositions durcissables en deux parties presentant des proprietes d'adherence ameliorees sur divers substrats
GB2068397A (en) * 1980-01-21 1981-08-12 Toray Silicone Co Silicone compositions for adhesion and method for adhering silicone rubber to a substrate
EP0044673A1 (fr) * 1980-07-11 1982-01-27 Toray Silicone Company Limited Promoteurs d'adhérence contenant des résines phénylsiloxanes
EP0044672A1 (fr) * 1980-07-17 1982-01-27 Toray Silicone Company Limited Promoteurs d'adhérence à base d'une résine phénylsiloxane et d'un polysiloxane ayant des groupes vinyliques

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0306302A2 (fr) * 1987-09-04 1989-03-08 Cogent Limited Composition et procédé pour la fabrication d'un revêtement résistant au rayage
EP0306302A3 (fr) * 1987-09-04 1991-01-30 Cogent Limited Composition et procédé pour la fabrication d'un revêtement résistant au rayage
FR2629089A1 (fr) * 1988-03-24 1989-09-29 Rhone Poulenc Chimie Diorganopolysiloxane porteur a la fois de radicaux vinyle et de radicaux organique epoxy-fonctionnel
EP0336854A1 (fr) * 1988-03-24 1989-10-11 Rhone-Poulenc Chimie Diorganopolysiloxane porteur à la fois de radicaux vinyle et de radicaux organiques époxy-fonctionnel
EP0500115A1 (fr) * 1991-02-21 1992-08-26 Dow Corning Corporation Composition de silicone pour couches primaires
GB2316079A (en) * 1996-08-13 1998-02-18 Gen Electric Primer composition for one-part RTV compositions
FR2752424A1 (fr) * 1996-08-13 1998-02-20 Gen Electric Composition pour couche primaire et procede pour ameliorer l'adherence des silicones a un support
GB2316079B (en) * 1996-08-13 2000-10-11 Gen Electric Flame retardant polyester composition
WO2008013521A1 (fr) * 2006-07-25 2008-01-31 Hewlett-Packard Development Company, L.P. Systèmes d'imprimante laser, éléments de transfert intermédiaire, couches primaires pour éléments de transfert intermédiaire et compositions de couches primaires
US10072181B2 (en) 2006-07-25 2018-09-11 Hewlett-Packard Development Company, L.P. Laser printer systems, intermediate transfer members, primer layers for intermediate transfer members, and primer layer compositions

Also Published As

Publication number Publication date
DE3564281D1 (de) 1988-09-15
JPH0548261B2 (fr) 1993-07-21
EP0164879B1 (fr) 1988-08-10
CA1244182A (fr) 1988-11-01
JPS60233153A (ja) 1985-11-19
US4598134A (en) 1986-07-01

Similar Documents

Publication Publication Date Title
EP0164879B1 (fr) Compositions de polysiloxanes pour couches primaires
KR930010439B1 (ko) 접착용 프라이머 조성물
US4082726A (en) Curable organopolysiloxane compositions with improved adhesion
EP0061871B1 (fr) Composition d'apprêtage pour adhésion de caoutchouc de silicones et méthode d'application
US4157357A (en) Curable two-part silicone rubber compositions with improved adhesion properties
US4033924A (en) Heat curable organopolysiloxane compositions containing adhesion additives
EP0051363B1 (fr) Promoteurs d'adhésion
US4332844A (en) Silicone compositions for adhesion and method for adhering silicone rubber to a substrate
US4742103A (en) Curable organopolysiloxane compositions exhibiting improved adhesion
US4737562A (en) Self-adhering polyorganosiloxane elastomer compositions and method for preparing same
US4808483A (en) Primer compositions
US5468805A (en) Room-temperature-curable organopolysiloxane composition method for its preparation
EP0431881A2 (fr) Matière textile ayant une couche de revêtement de caoutchouc de silicone autocollante
JPH0848963A (ja) シリコーン系感圧接着剤組成物
US4436787A (en) Durable primer composition
US5928794A (en) Addition curable composition having self adhesion to substrates
US5561184A (en) Room temperature curable silicone composition
JP3935530B2 (ja) プライマー組成物および接着方法
EP0685547A1 (fr) Compositions pour lier des élastomères organosiloxanes aux polymères organiques
EP0044672B1 (fr) Promoteurs d'adhérence à base d'une résine phénylsiloxane et d'un polysiloxane ayant des groupes vinyliques
JP3539167B2 (ja) プライマー組成物
JP7485049B2 (ja) 熱ラジカル硬化可能なオルガノポリシロキサン組成物、該組成物で接着、コーティング又はポッティングされた物品、及び該組成物の硬化物を製造する方法
KR930009217B1 (ko) 실리콘 고무용 접착제
US6306999B1 (en) Room temperature curable organopolysiloxane composition
EP0221644B1 (fr) Adhésion d'une masse d'étanchéité à base de siloxane

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): BE DE FR GB IT NL

17P Request for examination filed

Effective date: 19860520

17Q First examination report despatched

Effective date: 19870109

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR GB IT NL

REF Corresponds to:

Ref document number: 3564281

Country of ref document: DE

Date of ref document: 19880915

ITF It: translation for a ep patent filed
ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
ITTA It: last paid annual fee
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19980313

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19980316

Year of fee payment: 14

Ref country code: FR

Payment date: 19980316

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19980430

Year of fee payment: 14

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19980513

Year of fee payment: 14

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990503

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990531

BERE Be: lapsed

Owner name: TORAY SILICONE CY LTD

Effective date: 19990531

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19991201

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19990503

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20000131

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 19991201

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20000301

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST